


Descent to Hell

by samsbestgirl



Category: Supernatural
Genre: Action/Adventure, Angst with a Happy Ending, BAMF Dean Winchester, Based on Dante's Inferno, Bottom Sam, Denial of Feelings, First Kiss, First Time, Going to Hell, Love Confessions, M/M, Mythology References, Not Canon Compliant, Protective Dean, Quests, Sam Winchester in Hell, Self-Discovery, Sibling Incest, Top Dean, Underworld
Language: English
Status: In-Progress
Published: 2020-02-19
Updated: 2020-02-20
Packaged: 2021-02-27 23:41:48
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 1
Words: 1,780
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22804258
Author URL: https://archiveofourown.org/users/samsbestgirl/pseuds/samsbestgirl
Summary: To save Sam, Dean must make it through the Nine Circles of Hell.After some low-ranking demons kidnapped Sam to make him an offering to Lucifer, Dean will do anything to get him back. He agrees to return to Hell and retrieve his brother. Easier said than done when he's required to pass a different test in each of Hell's circles. Will he get to his brother fast enough? And what is he going to lose in the process?
Relationships: Dean Winchester/Sam Winchester
Comments: 8
Kudos: 25





	Descent to Hell

**Author's Note:**

> The story is not canon-compliant. It takes place sometime in season 4 though, after Dean's return from Hell.
> 
> This is based on Dante's book: Inferno.
> 
> Also, English is not my first language so mistakes can and probably will be found. I apologize for that.
> 
> Rating: NC-17 overall (I mean, the epilogue will probably be full-on smut)
> 
> Oh and this is my second try at writing a multi-chapters story so I hope it'll fare better than the last. I really want to complete this one though!
> 
> ENJOY IT!

**"The path to paradise begins in hell." - Dante Alighieri**

Dean loudly knocked three times on the run-down door in front of him. It was bright red, probably painted over too many times to still appear new to the eye, not that Dean paid any mind to these kinds of details, although he couldn't help but appreciate the irony. Red door to Hell and all that. _Fucking funny._ He waited patiently, his gaze wandering around the narrow street, dimly lit by the poorly concealed neon sign proclaiming in bright, yellow lettering "ROAD TO HELL." Dean briefly questioned whether the business's good. 

After a few minutes of dead silence, the door opened, revealing a short middle-aged woman, thin, an eye-patch covering half of her face, the other shadowed in the dark glow coming from inside. She looked him over, assessing him with her cold, calculated gaze. Dean smiled forcingly, raising his arm and allowing her to see the coin Anne gave him. She told him he might need it. The woman's eyes widened and she stepped aside, holding the door open for him to enter. Dean threw a last look over his shoulder, silently saying farewell to his baby, expertly hidden in plain sight, and then he went past the creepy lady inside.

The door closed quietly behind him, sealing his fate. 

He hadn't known what to expect once he got here, but this wasn't it. It looked exactly like a normal tattoo shop, darkly lit, a leather-bound chair in the middle of the room and a mahogany desk in the corner, files scattered all over it, as you would see on a secretary's work table. Well, Anne told him it might seem plain and not overly supernatural to the human eye, but he hadn't completely believed her, even though she was the expert. Now, looking around, he could see nothing out of the ordinary. _Demons and their bureaucracy..._

He turned around to face the freaky woman but he was startled to find her already in his face, her tiny hand snatching the coin from him with practiced ease and finesse. She analyzed his face carefully, then tossed the coin in the air which made it magically disappear into thin air. Witches. Figures.

"With whom do I have the pleasure of speaking?" She asked although Dean had the sense she knew exactly who he was. 

"I'm Dean. Winchester. You probably know why I'm here." He didn't have the time for games. Every minute he spent making small talk with petty witches cost his brother more pain. 

The woman laughed, throwing her head back and clutching her stomach hard. "Of course I know why you're here, Dean Winchester. The entire population of hell knows why you're here. The question is, do _you_ know what you're getting yourself into?" 

Dean bit back a snarky response, "Yeah, go to Hell, save my brother, get the hell out of Dodge. Simple enough." 

"Oh, then you must be a fool. It's never 'simple enough'. You out of all people should know that." She smirked, licking her lips slowly. "Have you ever heard of the Nine Circles of Hell?"

"That crap students learn about in college?" He made a face, scratching his chin with a hand. 

The woman raised an eyebrow at him, silently contemplating the best course of action. "That crap, as you eloquently put it, is very real. You'll find out just how real it is." 

Dean couldn't help but think she was threatening him. "Could you be more cryptic than that?"

"That's all you need to know for now." The answer was short, curt, the conversation over. Dean knew it was pointless to try and pull more information out of her. 

He sighed and watched her move around the messy desk, pressing a huge hidden black button already carved into the wood. He wanted to comment, to ask more, but he held his tongue, not-so-patiently waiting to see what was next. A gust of cold air crept up over the back of his neck and goosebumps instantly broke over his skin. The presence behind him was like ice incarnated and he didn't want to be anywhere near it the moment he sensed it.

But he needed to. For Sam.

He slowly turned around. The man was tall, taller even than Sammy, and he wore a black robe, the hood pulled over his face, hiding it from view. He looked like a hollow shell. Dean took a deep breath in and asked in a quiet tone, "You must be Charon." He knew enough mythology to realize it when he met the ferryman of the dead. He just never thought he'd get to see him up and personal.

The woman made her way to them, coming to stand beside the ferryman. "He will carry you across the rivers and through the Nine Circles of Hell. Whatever you do, listen to him. If you lose him, you'll be required to find your way to Lucifer alone. And I wouldn't recommend that."

"Wait. Through the Nine Circles of Hell? You can't be serious." He huffed, expecting the punch line, but both the woman and Charon looked dead serious. "What about directions? What do I have to do once I get there?" He asked, frustrated. 

"I told you already. You'll know when the time has come."

"Well, lady, that's not comforting at all." 

_Sam, wherever you are, just know you're an idiot. I'm never letting you out of my sight again._

"It's the only way to Lucifer. And he has your brother. The demons who took him made sure of that. Now, I'll ask you again, are you sure you want to do this? You can turn around and forget any of this ever happened, make a life for yourself. Your brother's gone. There's no guaranty that you'll save him even if you do make it through the Circles intact."

"No. That's not an option. I _will_ save my brother. No matter what. They can't do anything to me that'd be worse than a life without Sam." Dean responded, no hesitation.

The woman seemed impressed, a little smile tugging at the corner of her lips. "That's noble of you. Be aware though, there are great challenges ahead, keep your eyes open, don't trust anyone and no matter what you do, remember who you are, what you're there for. If you lose yourself, then it's over. For you and for your brother." 

Dean swallowed hard, running his tongue over his lips. "Thank you." He said simply, appreciating her advice. He was sure he'll come to need it.

Charon reached out his hand, pointing at a back door Dean's failed to see when he'd checked the room. He didn't trust this guy, mythical entity or not, so sue him if he was a little reluctant to follow him. It's not every day the ferryman of the deceased leads you to the underworld. 

"Be careful," the nice lady said, waving at him. "I hope you save your brother."

Dean smiled and waved back, nodding at her, then he caught up with Charon. He passed through the door, not looking back.

It was like he stepped into another world. Which he kinda did.

The river Styx spread out imposing and threatening in front of him, one little boat floating steadily, waiting for them to board. It dawned on Dean then that he was back in Hell. In literal Hell. He tried to keep his breathing in check, to not give in to painful memories, closing his eyes for a second to ground himself.

Sam was counting on him. Fear will only hold him back. He had to get to his brother and fast, God only knew what he was going through...

That was one more thing Dean couldn't think about. If he sat down and wondered what could be happening to Sam right that second, he'd surely lose his mind with worry. He'd remain petrified, useless, crying for the brother he failed to protect. His baby brother... God.

_Please, let him be okay._

He slowly opened his eyes, not allowing his mind to drift even further and noticed Charon's already boarded and was waiting patiently for him. Dean wondered if he ever spoke and if he was always so calm and collected. He was probably going to find out.

His presence still gave him chills but he fought against his survival's instincts and crossed over onto the tiny boat. It gave a little under his added weight and Dean cursed quietly under his breath. "Dead people are usually lighter," Charon said, startling Dean.

He snapped his head in the direction of the sound, his eyes wide and spooked. That was the creepiest tone of voice he has ever heard. He'd gladly spend this whole trip in silence, thank you very much. With the hood in the way, Dean couldn't match the voice with a face and he wasn't sure he even wanted to anymore. Better he didn't know how Charon really looked like.

"Good to know," he responded, quietly whistling. "Where to now?"

Charon tilted his head to the side, "Limbo."

"Well," Dean slapped his hands over his knees and sat down, making himself as comfortable as he could in the cramped space of the boat. "That doesn't sound ominous at all."

His guide didn't say anything more, he only picked up his pole and put the boat in motion. "Can I ask you something?" Dean said. He didn't wait for an answer. "Shouldn't I have paid a fee or something?" At least that's what he remembered for the little he's heard about greek mythology. 

"You already did," he boatman said curtly. "The coin Shynaia took from you."

"Oh," breathed out Dean. Guess Anne knew what she was talking about. He was glad Bobby recommended her to him. A specialist, he called her.

Nothing more was to be said so Dean looked out ahead and wondered what awaited him. He wasn't really scared, not for himself anyway. He only worried about what would happen to his brother if he was to fail.

So that wasn't an option. He would see this thing through. Sam will be back to him, by his side, fighting the good fight together. Dean would make sure of that. Because if he couldn't get his Sammy back, Earth didn't hold anything for him anymore. He'll be damned -besides his brother, as he should be- forever in Hell and honestly, that beat whatever eternity waited for him in Heaven without the boy he raised. If he couldn't have Sam, then he didn't want anything else.

His mind buzzing with worry and uncertainties about their futures, Dean began his descent to Hell.

**Author's Note:**

> Comments are love and motivate me to keep writing, so please don't refrain from letting me know what you think.  
> I'll update as soon as I can!


End file.
